No. 69: Your Style Guide is Here--This is What to Wear to Survive Ugly Winter™

It’s here, don’t be afraid, I've got your back at all price points.

This is, without a doubt, the most bizarre and offensive time of the year to shop. As I write this, it’s ten degrees outside. Ten. I live in Dallas, Texas just in case anyone needed that reminder. And on this day, I’ve received no less than three emails from brands saying their spring collections and vacation edits have launched. I understand the way the garment industry works, I do. I’m not wagging my fingers and saying how dare you, but mayyybee I’m looking at the marketing team and asking…really? You took out your weather app for the nation today in their polar vortexes and blizzards and thought this is what they need??

Because I’d argue we have officially entered what I call Ugly Winter™. It’s not precious, Hallmark winter anymore. We don’t rejoice with every snowfall and hardly find ourselves giddy with sub 30° days. No, fam, we’re cold. We miss the warmth of the sun on our skin. We miss the sun, period. January and February are reserved for surprise sleet and snow that fades instantly to a gray-brown slush. It’s dark and sad and we’re in it until the bitter end. The long slog.

Hear me loud and clear: This is not a wise time to shop for the season. One, because when you seek out what you need, you’re met with pastels and sundresses and an endless sea of crop tops. Friends, please do not go shopping blindly—not even for a random sweatshirt on Amazon—without first answering some questions I have for you. It’s one of the sneakiest seasons, Ugly Winter™. If you’re not careful, you’re probably even more likely to overspend on your wardrobe than you are during the Holidays and here’s why:

you’re cold, you’re exhausted and you’re delusional.

Simple as that. The cold makes you think you need every sweater you see on your way to grab paper plates and Pull-Ups at Target, every skims “dupe” you see on Amazon and every coat your favorite influencer links on their trip to Aspen/Utah/Somewhere Cold and Magical.

You might need a couple things to get you through this stretch, but you certainly don’t need seven. I promise.

The first question I always have to ask should go without saying, but I think we all often need the reminder— Do you have the money to spend on your wardrobe right now? The question isn’t “do you have money.” Nope. It’s do you have the money to spend on your wardrobe right now. Are you working towards a financial goal? Are you hemorrhaging money on an unexpected problem that you hadn’t plan for? Have you set a goal to spend less on impulse purchases? There are a million reason why the answer to these questions would make it clear that you’re not able to shop right now and if that’s the case, this post is strictly for inspiration in the wardrobe you already have.

If you do have some dollars to dedicate toward Ugly Winter™, here are the remaining questions for you:

1. Do you live in a place where you’ll get at least two more months out of Ugly Winter staples?
2. Do you have anything in your closet that can fill that gap you might have forgotten about?
3. Can you get by without the item you’re aching to purchase?
4. Is this something you want as a quick fix or a long standing staple and investment piece you hope to last for years to come?
5. Would the money you’ll spend better serve your Spring wardrobe than your Ugly Winter wardrobe?

Smartest Investments for your Ugly Winter™ Wardrobe:

Here are the 5 things I’d actually recommend investing in if you’re in a climate where you need to stay warm well into March (or April) that are worth adding to your wardrobe.